The Best of Frenemies

In 1997, Steve Jobs took the stage at Macworld in Boston. It was one of his first public appearances after returning to the ailing company he’d left more than a decade earlier. Halfway through his presentation, he dropped a bombshell: Apple was teaming up with Microsoft. The audience of Apple fans jeered and booed. Microsoft was Apple’s archenemy; Bill Gates was evil incarnate. There wasn’t a worse partner for Apple. Gates appeared at the event via satellite, his face looming high over Jobs like Big Brother in Apple’s iconic 1984 TV ad.

It seemed an unlikely match, but in fact Jobs and Gates went way back. They met in the early ’80s, when Gates was one of the first software developers for the Macintosh. As Gates noted while paying tribute to Jobs after his death, they would go on to spend half their professional lives in each other’s orbit. They even went on double dates together.

Gates was an early evangelist of the Mac and enthusiastically boosted the platform. Jobs was so pleased, he lent Gates a prototype machine to work on. Gates called it SAND (Steve’s Amazing New Device). Soon, though, both companies were suing each other over copyright issues. The lawsuits led to nearly a decade of acrimony, insults, and taunts.

“The only problem with Microsoft is they just have no taste,” Jobs once said. “I don’t mean that in a small way, I mean that in a big way.”

Jobs noted that Gates would “be a broader guy if he had dropped acid once or gone off to an ashram when he was younger.”

Asked about Microsoft’s success, Jobs said: “I have no problem with their success. They’ve earned their success for the most part. I have a problem with the fact that they just make really third-rate products.”

Gates returned the insults. Responding to Jobs’s return to Apple, he said: “What I can’t figure out is why he is even trying. He knows he can’t win.”

But contrary to his reputation, Gates was mostly an ally—and sometimes a savior—to his long-running rival. Macworld Boston wasn’t the only time he bailed Jobs out. In 2001, when Jobs desperately needed developers to support OS X, Gates agreed to create a version of Office for it. If he hadn’t, OS X could have been dead in the water.

The two tech titans were classic frenemies: joined at the hip, but often hacking at each other. Close but adversarial. Supportive and competitive.

In 2007, Jobs and Gates shared the stage at a tech conference to reminisce. Jobs joked that they had been secretly married for 10 years, and praised Gates’s philanthropy. “I think the world’s a better place because Bill realized that his goal isn’t to be the richest guy in the cemetery, right?”

After Jobs died, Gates was one of the first to eulogize him. “Steve and I first met nearly 30 years ago and have been colleagues, competitors, and friends over the course of more than half our lives,” he said in a statement. “For those of us lucky enough to get to work with him, it’s been an insanely great honor.”